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    Dutchess County, NY Short Term Rental Properties for Sale

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    Brooklyn, NY New York, NY Bronx, NY
    Versatile Multi-Unit Property in Red Hook
    $899,000
    3,500 SF
    Versatile Multi-Unit Property in Red Hook

    32 Old Route 199, Red Hook, NY 12571

    Two-unit property on four acres near Red Hook village.
    • Flexible living arrangement: Easily converts between two separate units and a single‑family home.
    • Income potential: Unit one generates long‑term rental income, and unit two has a successful Airbnb track record.
    • Private and secluded: Located at the end of a long driveway on four acres with mature trees and gardens.
    • Prime location: Short stroll to the village, offering both seclusion and convenience.
    • Multiple outbuildings: Includes a cottage, former sheep barn, and chicken coops, providing functional and charming spaces.
    Updated: Apr 22
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    Ranch Duplex with Wood-Burning Fireplaces
    $899,000
    4.00 Acres
    Ranch Duplex with Wood-Burning Fireplaces

    32 Old Route 199, Red Hook, NY 12571

    Two flexible living units on four private acres, with outdoor decks and historic outbuildings for everyday comfort or conversion.
    • Four‑acre property at the end of a long private drive with lawns, pastures, and lightly wooded areas
    • Two separate living units: Unit One has 4 bedrooms, 3 bathrooms, and a finished lower level
    • Unit Two has 2 bedrooms and 2 bathrooms and has a history as a short‑term rental
    • Each unit includes wood‑burning fireplaces and a wood stove
    • Outdoor features include expansive decks and porches plus a studio cottage, former sheep barn with storage, chicken coops, and established garden areas
    Updated: Apr 20
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    Turn-Key Estate with Rental History
    $2,500,000
    4.30 Acres
    Turn-Key Estate with Rental History

    Georgian estate with cottages, renovated for vacation rentals.

    18 Stagecoach Ln, Amenia, NY 12501

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    Based on your search, we've compiled 3 Potential Opportunities for your consideration. Besides 3 Active listings in Dutchess County, NY, we suggest exploring several alternatives:

    Dutchess County, NY Short Term Rental Properties Market Trends and Statistics

    Explore 3 short term rental properties for sale in Dutchess County, NY, showcased through 3 active listings on our real estate platform. These investment opportunities span a total of 3,500 square feet of properties for sale, with an estimated market value of $899,000.

    Sale prices for short term rental properties in Dutchess County, NY start at $899,000, averaging $899,000, and reaching up to $899,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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